Urea → methyl 4-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-3-methyl-1-piperidinecarboxylate

HRID 1729800Notes

Reaction equation

HRID 1729800 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:11]1[CH3:20].N[C:22](N)=[O:23]>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:11]3[CH3:20])[C:22](=[O:23])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 21500239HCID 21500239, compound

Product 1

HCID 21500273methyl 4-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-3-methyl-1-piperidinecarboxylate

Procedure

A mixture of 30 parts of methyl 4-(2-amino-4-chlorophenylamino)-3-methyl-1-piperidinecarboxylate and 10 parts of urea is stirred and heated at 160°-180° C (oil-bath) for 3h. 30. The reaction mixture is cooled and the product is extracted with methylbenzene. The extract is washed successively with water, with a diluted hydrochloric acid solution and again with water, dried, filtered and evaporated. The oily residue is crystallized from a warm mixture of 2,2'-oxybispropane and a small amount of 2-propanol. After cooling, the product is filtered off and dried, yielding methyl 4-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-3-methyl-1-piperidinecarboxylate; mp. 196.2° C.

Workup

  1. temperatureheated at 160°-180° C (oil-bath) for 3h
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed successively with water, with a diluted hydrochloric acid solution and again with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is crystallized from a warm mixture of 2,2'-oxybispropane
  9. temperatureAfter cooling
  10. filtrationthe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-757f53dd0c844a7cbd07375c32fe3f35
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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